1-propoxyindole | 160725-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-propoxyindole
• 英文别名: 1-n-propoxyindole
• CAS: 160725-09-7
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: YCSXRBLKXNHOFV-UHFFFAOYSA-N

物化性质

• 沸点：
  270.0±23.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-propoxyindole 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 3-(1H-indol-3-yl)-4-(1-propoxyindol-3-yl)pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis, and Cytotoxic Activity of Nind-Alkoxy Derivatives of Antibiotic Arcyriarubin and Dechloro-rebeccamycin Aglycon.

  摘要：

  DOI：

  10.7164/antibiotics.55.768
• 作为产物：
  描述：

  吲哚啉 在 sodium tungstate (VI) dihydrate 、 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-propoxyindole
  参考文献：
  名称：

  Discovery, synthesis, and optimization of an N-alkoxy indolylacetamide against HIV-1 carrying NNRTI-resistant mutations from the Isatis indigotica root

  摘要：

  From an aqueous decoction of the traditional Chinese medicine "ban lan gen" (the Isatis indigotica root), an antiviral natural product CI - 39 was isolated as an NNRTI (non-nucleoside reverse transcriptase inhibitor) (EC50 = 3.40 mu M). Its novel structure was determined as methyl (1-methoxy-1H-indol-3-yl)acetamidobenzoate by spectroscopic data and confirmed by single crystal X-ray diffraction. Through synthesis and structure-activity relationship (SAR) investigation of CI - 39 and 57 new derivatives (24 with EC50 values of 0.06-8.55 mu M), two optimized derivatives 10f and 10i (EC50: 0.06 mu M and 0.06 mu M) having activity comparable to that of NVP (EC50 = 0.03 mu M) were obtained. Further evaluation verified that 10f and 10i were RT DNA polymerase inhibitors and exhibited better activities and drug resistance folds compared to NVP against seven NNRTI-resistant strains carrying different mutations. Especially, 10i (EC50 = 0.43 mu M) was more active to the L100I/K103N double-mutant strain as compared to both NVP (EC50 = 0.76 mu M) and EFV (EC50 = 1.08 mu M). The molecular docking demonstrated a possible binding pattern between 10i and RT and revealed activity mechanism of 10i against the NNRTI-resistant strains. Copyright (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112071

文献信息

• Synthesis and study of neoscorbigen and its analogs
  作者：V. I. Mukhanov、M. M. Kaganskii、A. A. Sorokin、S. G. Antonyan、G. V. Tananova、L. L. Mikhailevskaya、A. S. Kinzirskii、M. N. Preobrazhenskaya

  DOI：10.1007/bf02219244

  日期：1994.7